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Explore Woodstock

With a surprisingly large arts community, rolling green hills, and friendly locals, the small and picturesque town of Woodstock has it all! The primary street that hosts a row of boutiques and charming restaurants is known as Tinker Street, but don't limit yourself to this one area. There are plenty of things to see and do across the entire town.

Here are just a few additional suggestions of things to do in Woodstock:

-Shawangunk Mountains: This mountain range attracts people from all over the area with its rock climbing, hiking, and camping options.

-SweetHeart Gallery: Overlooking a beautiful waterfall, this popular local gallery features artwork and crafts pieces from some of the best artists in the region.

-Karma Triyana Dharmachakra Tibetan Buddhist Monastery: This beautiful and serene monastery is the perfect place to spend an afternoon learning about Buddhism or just simply clearing your head.

For those looking to attend local events and festivals, head to Ulster County, a short drive from Woodstock. In Ulster County you can cheer on the competitors participating in the Shandaken Primitive Biathlon in January, watch the boat rally on the Wallkill River at the New Paltz Regatta in May, or take home a piece of art from one of the best artists in the region at the Woodstock-New Paltz Art and Crafts Fair in September.

Luckily, there's a vacation rental available in Woodstock that has everything you are looking for in a getaway home. Book a luxury condo downtown or rent a secluded cabin in the woods just steps from the mountains for an unforgettable vacation experience.

If you're looking to explore the surrounding area, there are several other towns just outside of Woodstock that make for great day trips. The busy college town of Binghamton and the rolling fields of Oswego can both be reached within an hour by car.

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Book on FlipKey(8)

Reviewed(12)

PreviousNext property

$150 / night

$150

Located right in the middle of Woodstock, this recently renovated cottage with a cozy, open floor plan affords you both privacy and convenience. There's no need for a car. Walk to everything, including the NYC bus stop, Woodstock's unique shops and galleries, or hiking trails. Cook your own meals in the well equipped …

Lovely property in a great location

Left on Mar 27, 2013 for a stay in October 2011

Beautiful & charming are the words that come to mind when describing this cozy cottage. It's right in the heart of Woodstock...you can literally walk to everything the town has to offer, yet it's quietly tucked away so you also get a sense of privacy in a serene setting. We are looking forward to coming back year after year.

$350

Charming house In a compound of two houses in the green rolling hills of Bearsville. It is 5 mins to Woodstock Village Green. Heated, saltwater pool, hot tub, fireplace. Renovated in a relaxed lodge style. Local Spa 5 mins away.
To relax your mind spirit and body
Come and rejuvenate yourself in the relaxing …

Epic property and very helpful hosts

Left on Aug 09, 2012 for a stay in July 2012

My girlfriend and our dog stayed for a weekend in July and had an amazing time. From our initial inquiry to even after our stay Sarah was very responsive and helpful. The property is amazing and very well kept. Upon arrival, she met us with some fresh fruit and Prosecco and helped us get situated. It was one of the hottest weekends of summer and we knew that it had no aC and it was fine at night …

$195 / night

$195

Come for the perfect romantic getaway. Newly renovated, one bedroom, luxury cabin, in the heart of Woodstock. Secluded and private on 6 acres of forest and open land. Soak in the hot tub and watch deer meander, wild turkey and woodpeckers. Large deck to BBQ and entertain on. Stay connected with high speed (wi-fi) …

A place to do everything, or nothing

Left on Oct 11, 2011 for a stay in October 2011

I must confess, that I did not expect much, hearing from a local friend who drove by the property. While previous vacations advertised themselves as located in Woodstock, this one truly is. Took us an hour and fourty minutes from manhattan, door to door. While it looked a little quirky at first sight, with an extension above the living room, once we entered we realized that it serves as a giant …

$400

Private, modern home centered around a geodesic dome has every luxury you need for a city reprieve. The home is situated on 2 acres off a private road within walking distance to the Village of Woodstock, restaurants, shops and galleries.
Each bedroom has its own full bath with a steam shower in the master …

Dome!

Left on May 01, 2013 for a stay in February 2013

This house is amazing! Simultaneously roomy and cozy because of the different spaces and architectures. Flw fans make sure to pick this home and read the wwner's cool collection of literature on his architecture. Woodstock is a fun place full of interesting people and shops and great places to eat and the Catskills are beautiful year round. The manager for this home was awesome to work with.

PreviousNext property

$225 / night

$225

Located at the heart of woodstock (on Ricks Rd) this newly built cabin is a dream gateway. Spacious, with all modern amenities, free wi-fi, cable TV, Netflix enabled, Gas fireplace, whisper quiet AC, romantic outdoor hot tub, large covered deck with infrared BBQ grill. Great lounging chairs to take in the views, …

PreviousNext property

$375 / night

$375

This special home is a converted barn with the original 1790's foundation. We want our guests to feel at peace and have a relaxing vacation! The house is filled with unique collectibles and folk art. You'll find an eclectic collection of original paintings throughout the house. Each room has a delightful, unique charm…

PreviousNext property

$220 / night

$220

Our beautiful country home boasts cathedral ceilings, skylights and an open floor plan. Large covered deck (with hot tub) off the living room makes it perfect for entertaining and outdoor dining rain or shine! Only 30 min. from Hunter mountain skiing and many swimming holes. Your kids will love the outdoor jungle gym …

$195 / night

$195

A large and cozy private barn, in rural setting, on five acres of wooded land, with a stream outside your window and a larger stream at the front of the property. Comfortable, with modern accommodation and beautiful artistic details. A perfect place for a peaceful, romantic getaway. A year-round, completely private …

Excellent, romantic place

Left on Apr 10, 2011 for a stay in April 2011

My partner and I spend the most amazing weekend at the barn. It was cozy, great views from every window, love waking up in the morning seeing the woods and hearing the bubbling spring outside. The bed was comfortable, and the place was very clean and quiet. Being in the hot tub under the starts was amazing!!! we're planning another visit in the fall.

$295

Immaculate Woodstock Craftsman luxury home on secluded 7 acres with private stream, pool and hot tub. Top of the line brand new furnishings from ABC Home. Ideal for hiking, biking, swimming and nature explorations. Property backs up to Comeau Nature preserve and yet is only 5 min away from the village of Woodstock …

Secluded mini-estate close to town

Left on Sep 27, 2014 for a stay in August 2014

This place is great, spacious and secluded but just minutes from Woodstock. At the end of a small road with a stream running along side the property has a great feel to it. We were two couples and one child and had loads of room to spread out. The "loft" bedroom in particular was really pretty neat.

The kitchen is a little small, but very workable for two persons. The hot tub was …

PreviousNext property

$225 / night

$225

On the border line of Woodstock & Saugerties. 4.5 miles from the center of Woodstock village.
Drive down a private country road to Saddle Hill where you will find a completely secluded retreat nestled, on 2.5 acres, between the Catskill Mountains and rolling fields.
Beautifully renovated, spacious contemporary home …

Simply the best!

Left on Jul 07, 2010 for a stay in May 2010

Before we even explored the beautiful house and the perfect location, we thought 'We are home'. This wonderful property is possibly the nicest, most pristine clean and convenient house we've had the pleasure to stay in. It is wonderfully furnished, comfortable and has everything you could want for a perfect vacation. This is not your standard 'rental'. This is a fantastic home and we had an …

$225

Located in the heart of Woodstock (Glasco Tpyk & Ricks Rd.) this cabin is the perfect romantic getaway. With 6 acres of of forest and open land as your back yard.
Newly renovated, 2 bedrooms 1 bath, Wood-burning fireplace, private hot tub, a deck with (infrared) gas BBQ grill. High speed (wi-fi) internet …

Amazing Experience

Left on Jun 06, 2013 for a stay in March 2013

We stayed at the cabin on March 27th-29th with our 2 sons and we fell in love with it!
The place is perfect! The bedrooms are cozy, the kitchen is fully equipped, the outdoor tub is a real treat, and there was enough space in the living room for the kids to play and watch Dvds.
We really liked the fact that it's close to Woodstock but also quiet and relaxing. You can take a nice walk; drink …

PreviousNext property

$255 / night

$255

Woodstock Holistic welcomes you to the Catskill Mountains and the Hudson Valley. We are an intimate bed and breakfast dedicated to wellness and serenity.
Experience a holistic renewal in the tranquil setting of our guest suites. Cozy up and discover distinctive characteristics that create a unique oasis. Every suite…

Perfect Location, Hidden Gem

Left on Aug 27, 2014 for a stay in July 2014

We stayed with our two grown children in the cabin over a long weekend in the summer. The house at first sight is somewhat quirky: tall with a large outdoor porch on the second floor. All of us were looking forward to spend some quality time together, but also were concerned about privacy. To our delight the second floor proved to be a huge master suit with it’s own outdoor space and totally …

$250

Charming Guest House in a compound of two houses In the rolling green hills of Bearsville, 2 miles from Woodstock Village Green. Brand new heated, saltwater, in-ground Pool and brand new Hot Tub, & fireplace. Renovated in a relaxed lodge style.
Please Note the guest house only rents out with the main house in the …

A modernly stylish and cozy getaway

Left on Apr 08, 2012 for a stay in March 2012

Loved our stay at the Bearsville Retreat this winter! The guesthouse is beautifully done with sunlight pouring in. Loved the fireplace, and being able to cook for ourselves in the kitchen. Its only a stone's throw from town though so if you dont feel like cooking, you can head into Woodstock. We were there in the winter so didnt swim in the pool but i definitely plan to be back there for another …

$200

The perfect getaway for family and groups, artists, writers, yoga and meditation lovers all are welcome.
Escape to a magical land- private and secluded with a hot tub out door, relax, hike, ski, meditate or create your new masterpiece.
The place invoke your imagination and stimulate your creativity.
located in the …

Relaxing Oasis

Left on Sep 21, 2011 for a stay in September 2011

An amazing beautiful and relaxing place! Both the house and property are wonderful - you are in the middle of the woods, yet several cute towns are just a short drive away. The beds are amazingly comfortable, the kitchen is well laid out, and the house has lots of open space for reading and relaxing. I can't wait to go back!

$200

Aspects Inn & Spa in the heart of Woodstock, NY offers a unique sensual retreat
with a two apartment 2 bedroom each w/ full kitchen and all amenities with direct access
to our indoor spa with 40' saline pool, ionized Jacuzzi and infrared sauna.
at the rate of $250 per night 1 couple…

A Great Place to Relax

Left on Oct 14, 2012 for a stay in October 2012

Aspects Inn & Spa is a relaxing oasis in Woodstock NY. The location is very convenient, just a short walk to the main street yet in a very quiet and private setting. The hosts, Sharon and Lio, thought of every detail to make for an enjoyable stay. The pool and spa are FANTASTIC.

PreviousNext property

$225 / night

$225

A unique newly renovated contemporary condo in a quiet townhouse community built in the midst of 25 wooded acres, and less than 5 minutes to Woodstock's village green. Enjoy peace and serenity in the sun-lit garden room, soak your cares away in the Jacuzzi tub in the main bathroom, embrace the warmth of the cozy …

PreviousNext property

$450 / night

$450

Welcome!
Note: We have plenty of 5 star reviews, please asks and we can send you a link.
This beautiful 2,000 sq. ft house is modern and clean. It sits on 3 acres of beautiful landscape and has a great 18 yard pool.
The house, recently renovated and conveniently located between Woodstock and Saugerties (5 minutes …

About Woodstock

With a surprisingly large arts community, rolling green hills, and friendly locals, the small and picturesque town of Woodstock has it all! The primary street that hosts a row of boutiques and charming restaurants is known as Tinker Street, but don't limit yourself to this one area. There are plenty of things to see and do across the entire town.

Here are just a few additional suggestions of things to do in Woodstock:

-Shawangunk Mountains: This mountain range attracts people from all over the area with its rock climbing, hiking, and camping options.

-SweetHeart Gallery: Overlooking a beautiful waterfall, this popular local gallery features artwork and crafts pieces from some of the best artists in the region.

-Karma Triyana Dharmachakra Tibetan Buddhist Monastery: This beautiful and serene monastery is the perfect place to spend an afternoon learning about Buddhism or just simply clearing your head.

For those looking to attend local events and festivals, head to Ulster County, a short drive from Woodstock. In Ulster County you can cheer on the competitors participating in the Shandaken Primitive Biathlon in January, watch the boat rally on the Wallkill River at the New Paltz Regatta in May, or take home a piece of art from one of the best artists in the region at the Woodstock-New Paltz Art and Crafts Fair in September.

Luckily, there's a vacation rental available in Woodstock that has everything you are looking for in a getaway home. Book a luxury condo downtown or rent a secluded cabin in the woods just steps from the mountains for an unforgettable vacation experience.

If you're looking to explore the surrounding area, there are several other towns just outside of Woodstock that make for great day trips. The busy college town of Binghamton and the rolling fields of Oswego can both be reached within an hour by car.

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